Help! My Stepsister Is Living a Reckless Double Life.

Dear Prudence is Slate’s advice column. Submit questions here.

Dear Prudence,

My stepsister and I grew up together from the age of 10, and I consider her a sister and a friend. She is smart, talented, charming, and pretty. She’s also loving to her people and is big on being there with practical support when things are hard for family or close friends. She’s also a serial cheater and “other woman.” It seems like she’s only interested in men who are in relationships. It started in our teens and I always hoped she’d grow out of it from the consequences if nothing else, but nothing has changed. When I’ve talked to her about it before she just brushed me off and said she’s in love and that it’s all worth it.

We’re in our late 20s now and she’s actively pursuing a guy who is married with a new baby, and her boyfriend understandably broke up with her when he found out. I can’t reconcile this with who she is in other ways. She’s hurting people. Her parents seem to have an implied agreement never to bring it up, and her friends have tried and failed. My brother says to leave it alone but it really bothers me that I’m close with someone who repeatedly does this. How do I have a more persuasive conversation with her?

—Sister, Sister

Dear Sister,

Oh gosh. Prudie’s letters this week are hitting a little close to home. I was not quite like how you describe your stepsister, but I regularly pursued inappropriate relationships in my 20s. One of them was with a widower twice my age with two children. You may think that’s not as bad as a married man with a baby, but I’m not sure it’s not worse; when I got bored, and realized that raising an 8 and 12-year-old (and possibly having a baby with someone who wasn’t so far from 60) was NOT cool and interesting, I vaporized on those two girls, not to mention their mess of a dad. Can you tell that with 20+ years of hindsight I am not proud of this? I am not proud of this.

But let me tell you what made me see the light on what I was doing, which was messing around smoking and drinking and eating french food with someone who was not in any shape or form to be messed around with. I was home for Thanksgiving that year, and my mom approached me in my childhood bedroom and asked if I was in a relationship with this person. She knew of him because I had talked about him in the past in the context of work, but recently I had mentioned him more. I confessed that I was. Let me just say that my mother strongly expressed her disapproval of this relationship. She kept it short and direct. It was a bit rougher than “I don’t approve of what you are doing,” but the message was received. Her opinion burrowed its way into my brain. I cared about what my mom thought even if I initially pretended I didn’t. And I couldn’t unhear her. I didn’t end my relationship because she didn’t like it. But I did because I saw myself through my mom’s eyes and realized that what I was doing was dumb and selfish.

So what I am trying to say is: I’m not sure having a big conversation with her about what she’s doing is all that useful. She will be defensive, and you will likely dig in, and it will be another impasse. But you could say: “Listen, I know I have brought this up before, but I just want to say one last time and then I will leave it alone: I don’t think the way you pursue relationships is healthy for you or the men you get involved with. Someone will always end up hurt in these situations, and it may often be you. I need to tell you because I love you. And I hope you will think about that.” Then you will have spoken up, and she will have heard you. And trust me, she’ll remember what you say.

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Dear Prudence,

I went through a bad breakup last spring with someone I really cared about. Everything had felt very loving and lovely until one day he changed into a completely different person. It felt like overnight he became distant and kind of mean after months of being extremely adoring, sweet, and thoughtful. When we ended things (I initiated, but he didn’t protest), I cried uncontrollably for weeks, even though I knew it was the right call. I couldn’t stay with someone I couldn’t trust!

It’s now officially been a year, and even though I remain sure that breaking up was the right decision, I’m somehow still not past it. I still think about him all the time, and I still frequently cry. I also have not felt attraction to another man since then, and I haven’t been able to be intimate with anyone else. Previously, I really enjoyed periods of being single, including having casual sex, but now I don’t even want to kiss anybody. I’ve stopped going on dates because they make me feel like something is wrong with me. I miss having crushes and feeling excited about new prospects. I miss feeling desirable and desirous. Why can’t I get over this? Am I broken?

—Can’t Move On

Dear Can’t Move On,

You are not broken. I promise. You just need more time. I remember someone telling me in my 20s that it took twice as long to get over relationships than the time they actually lasted. And because Prudie is feeling confessional this week, I will tell you: I had a relationship in my early 20s that was only a few months long but took me almost five years to get over. Five years! I tried to date, I tried to like other people, but it was impossible. I had been abandoned with a broken heart and it was terrible. Until it wasn’t! And then I went on to make all kinds of mistakes.

So, be patient. And when you are feeling even a little bit better, think about getting out there again, just because I think it’s good to keep the dating muscle flexing (and having sex is good, too, even if it’s not always amazing). I promise you’ll get your mojo back–probably when you least expect it.

Dear Prudence,

I (she/her, early 30s) am struggling with some weird and surprising emotions. My best friend (also early 30s) is stunningly beautiful. She’s generous, smart, and capable, and we deeply get each other. When we first met years ago we shared a mutual crush, but nothing ever happened. I’ve always said I’m grateful we never pursued anything since she’s such a wonderful friend.

A few days ago, she texted me that she has a new boyfriend. I told her how excited I was for her, but if I’m totally honest my stomach dropped reading her message. I thought maybe I was jealous of her finding a deeper connection (I’ve been having some existential dating anxiety lately), or that I was disappointed we won’t be single girls together anymore… But now I’m worried I’m just upset that her new person isn’t me.

I’ve never been jealous of her boyfriends before. We are devoted to each other, but we’ve always maintained some distance. I don’t want to risk such an important friendship. We’ve even talked about retiring together. I do not understand what has changed… How can I navigate these new (or maybe not so new) feelings? Help!

—Hopefully Overreacting

Dear Hopefully,

OK before I get to the heart of your letter, I have to address that you and your friend are in your early 30s and you are already discussing retiring together. It sounds like you are really close and care about each other and I love that!

But that depth of relationship means that changing it from something platonic to romantic is taking a risk. At the same time, given your past mutual crush and commitment to each other, maybe it’s one that would pay off? Prudie wants to tell you to throw caution to the wind, but from her own experience being on the receiving end of a confession of the kind you might be contemplating, it may complicate things in a way you aren’t considering. Meaning, how will you feel if she does not want to try being in a different kind of relationship with you? Can you handle putting yourself out there and not being able to control her reaction? When this happened to me, I was flattered by my friend and seriously thought about making the shift with her, but I wasn’t ready. (I was also 19 years old and it was 1994.) To her, it was a big deal and felt like a rejection from me, and it dinged our relationship badly enough that it didn’t really recover. I still miss her.

I would suggest sitting with your feelings for a little while and seeing if they grow in strength or wane. Now I have that REO Speedwagon song “Can’t Fight This Feeling” in my head. If you get to that point, where you just can’t fight the feeling anymore, you may have no choice but to say something. And I hope you get the response you’re dreaming of.

—Hillary

Three months ago, my wife and I had a calm disagreement over whether we should start a family. A few nights later, I replayed the conversation in my mind and got extremely angry about it. I went into the bathroom, flushed her birth control pills down the toilet, left the empty case on the counter, and then went back to bed. When I woke up in the morning, I was ashamed of myself, but I knew she had already seen what I’d done.